How To Get A Head.

This year, 2019, is the 200th anniversary of the first publication of the first installment of The Sketch Book of Geoffrey Crayon, Gent., by Washington Irving, which included his short story Rip Van Winkle. That other short story he’s known for, The Legend Of Sleepy Hollow, would be published in March 1820, but the residents of Sleepy Hollow, New York are already celebrating. They even got a more than twenty-year jump on celebrating when they changed the name of their town to Sleepy Hollow. It had been North Tarrytown, which sits, well, north of Tarrytown, the former home of Washington Irving. And that’s okay. Places change names all the time. You may have heard that old New York was once New Amsterdam, but that’s another story.
I was introduced to The Legend of Sleepy Hollow when I was a kid and saw the Disney animated version in school–several times, in fact. From kindergarten on it seemed like my teachers would show it at least once a year, usually around Halloween, or when they didn’t have anything planned, or when they wanted to keep us occupied long enough that they could slip out for a drink.
I loved the Disney version, which is really good, but Disney also has a history of playing fast and loose with the source material. (If Kipling had been alive in 1967 the cartoon of The Jungle Book would have made him roll over in his grave.) So I put off reading The Legend of Sleepy Hollow until college and it tickled me to see just how closely Disney hewed to the original, even keeping the ambiguous ending.
And Washington Irving turned out to be an interesting guy–more than just the answer to the question, “What is the name of our first president, Seymour?” He was born in 1783 when the United States was barely a country. Most Americans think of July 4th, 1776 as the day it all started, but there was a lot of back and forth and Amerixit took at least as long as Brexit probably will. George Washington had finished generalizing and was a few years away from presidenting when he met his namesake at a New York inn, which Irving would have been more excited about if he hadn’t been less than a year old.
At fifteen Irving left New York City because the Big Apple had the yellow fever, a little like Boccaccio’s Decameron before him or Poe’s The Masque Of The Red Death after him, and decided to tarry in Tarrytown where the countryside inspired some of his stories. He already knew he wanted to be a writer, and, after writing a slightly tongue-in-cheek history of New York City “from the beginning of time” under the nom de plume Diedrich Knickerbocker, and working as an editor, he went to Europe at thirty-two and stayed there for seventeen years. His family wasn’t happy, but he said he was determined to “return to the smiles, rather than skulk back to the pity of my friends.”
And he succeeded in spades. Before Fitzgerald, Hemingway, Stein, and others Washington Irving was the original American expat writer. And he wrote the original American Halloween story.
Charles Dickens has been credited with inventing the modern Christmas holiday–not the date, but the way we celebrate it now–but Irving, whom Dickens consulted about American Christmas traditions–did as much for Halloween, even if he doesn’t mention the holiday in The Legend Of Sleepy Hollow. Consider his description of Sleepy Hollow, a place sealed off from the rest of the world.

Local tales and superstitions thrive best in these sheltered, long-settled retreats; but are trampled under foot by the shifting throng that forms the population of most of our country places. Besides, there is no encouragement for ghosts in most of our villages, for they have scarcely had time to finish their first nap and turn themselves in their graves, before their surviving friends have travelled away from the neighborhood; so that when they turn out at night to walk their rounds, they have no acquaintance left to call upon…
The immediate cause, however, of the prevalence of supernatural stories in these parts, was doubtless owing to the vicinity of Sleepy Hollow. There was a contagion in the very air that blew from that haunted region; it breathed forth an atmosphere of dreams and fancies infecting all the land.

Sleepy Hollow is a primarily Dutch community, with traces of Native American history, but Ichabod is an outsider; from New York he works as the village schoolteacher. He wants in, though, and thinks the key will be the hand of Katrina Van Tassel, a beautiful village girl. The story not so subtly suggests, though, that Crane’s interest isn’t matrimony so much as inheriting the wealth held by Katrina’s father. When he arrives at a party he heads right for the food.

There was the doughty doughnut, the tender oly koek, and the crisp and crumbling cruller; sweet cakes and short cakes, ginger cakes and honey cakes, and the whole family of cakes. And then there were apple pies, and peach pies, and pumpkin pies; besides slices of ham and smoked beef; and moreover delectable dishes of preserved plums, and peaches, and pears, and quinces; not to mention broiled shad and roasted chickens; together with bowls of milk and cream, all mingled higgledy-piggledy, pretty much as I have enumerated them, with the motherly teapot sending up its clouds of vapor from the midst—Heaven bless the mark! I want breath and time to discuss this banquet as it deserves, and am too eager to get on with my story. Happily, Ichabod Crane was not in so great a hurry as his historian, but did ample justice to every dainty.

Sounds like a Halloween party, doesn’t it?
And then there are the ghost stories, especially that of the Headless Horseman, a Hessian soldier–Irving’s mix of characters also reflects the new American melting pot–who lost his head to a cannonball and goes riding at night in search of it. And yet he’s not entirely a scary character. Brom Bones, a rowdy village guy who’s competing with Ichabod for Katrina’s hand, says he met the Horseman one night, “and offered to race with him for a bowl of punch,” but the Horseman disappeared–as he always does–at the church bridge.
Ichabod’s not as brave or as skilled a rider as Brom and he disappears that night after meeting the Headless Horseman, but Irving leaves it to the reader to decide what happened.
As a kid watching the Disney version I thought Ichabod was the hero of the story–Tim Burton’s version, which plays fast and loose with the source material but is pretty good on its own, makes this even more explicit, turning him into a proto-Sherlock Holmes–and that his disappearance and possible death was tragic. As an adult I see him differently. He’s greedy, even a little sneaky, and wants to marry into a wealthy family so he can quit his job as a teacher. So what happens to him in the end? I think his head proved unworthy, but only the Headless Horseman could tell us, if he could speak.


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  1. Bill

    I love the treatment of the story and tradition here, and the excerpts you chose (especially the last one). Great read: entertaining, instructive…and makes me want to pull up one of the films to show my kids tonight! When I was quite young I got spooked by the film and worried the horseman would come for me, and wrap my head in the pillow when he took it off. To this day (no lie) I still don’t rest my head on the pillow.

    1. Christopher Waldrop (Post author)

      Thank you so much. When I read about the town of Sleepy Hollow turning into a Halloween wonderland to celebrate Washington Irving’s legacy I didn’t think that much about it but then just found my way into this. The Disney cartoon is probably the best version for kids–scary, but not too scary, and with plenty of humor to help.

  2. Ann Koplow

    All of us who still have heads know this was a very smart and entertaining post, Chris. I never saw the Disney version but I remember reading the Washington Irving and thinking it had a happy ending.

    1. Ann Koplow

      Just like the horseman is missing a head, that previous comment is missing a word: “story.”

    2. Christopher Waldrop (Post author)

      The ambiguity of the ending of Washington Irving’s story, which–spoiler alert!–is preserved in the Disney version does leave open the possibility of a happy ending. I think whether or not you read it as a happy ending says a lot about your feelings about Ichabod and there, too, is plenty of ambiguity.


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